A river surrounded by autumn-colored trees and a forested hill.

Find Hotels with a Pool in Stockbridge, MA

Check availability on Stockbridge Hotels with a Pool

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Oct 24 - Oct 25
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Oct 25 - Oct 26
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Oct 30 - Nov 1
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Nov 6 - Nov 8

Our top choices for Stockbridge hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$191 nightly
$214 total
Nov 5 - Nov 6
Total with taxes and fees
The Red Lion Inn
Indoor pool
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$109 nightly
$122 total
Nov 25 - Nov 26
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A multi-story building with a balcony, a pond with rocks, and a tree.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

4. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
$150 total
Oct 27 - Oct 28
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

5. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
$393 nightly
$439 total
Nov 7 - Nov 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A backyard with a swimming pool, surrounded by grass and trees.
A stone fountain surrounded by trees in a park setting.
Front of property
A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.

6. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
$383 nightly
$428 total
Nov 12 - Nov 13
Total with taxes and fees
The Inn at Stockbridge
A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.
A dining table set with a vase of flowers, a book, and cutlery.

7. Brook Farm Inn

Brook Farm Inn
Lenox
  • Dive into luxury poolside moments with a seasonal outdoor swimming area, vibrant bar service, and picturesque garden setting.
$199 nightly
$225 total
Oct 26 - Oct 27
Total with taxes and fees
Brook Farm Inn
A swimming pool with lounge chairs, surrounded by trees and a small building.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

8. Devonfield Inn B&B

Devonfield Inn B&B
Lee
  • Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
$95 nightly
$106 total
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A poolside area with lounge chairs and a pool.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden table with a green chair and a yellow vase with flowers.

10. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
$298 nightly
$333 total
Nov 9 - Nov 10
Total with taxes and fees
Prospect Berkshires
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub
4 stars
Spa
5 stars

Find out more about Stockbridge

Discover top Stockbridge attractions

In the charming town of Stockbridge, travelers can immerse themselves in a variety of delightful activities that highlight the region's unique character. Art enthusiasts will appreciate the cultural richness at local galleries, featuring works from both contemporary and classic artists. Stroll through the picturesque streets to enjoy the stunning architecture and vibrant landscapes, perfect for capturing memorable photographs. For those with a taste for history, engaging exhibits showcase the area's heritage, offering fascinating insights into Stockbridge's past. Outdoor lovers can explore the serene parks that beckon with walking paths and beautiful scenery, ideal for a leisurely afternoon picnic. Lastly, indulge in the local culinary scene where charming eateries serve up delectable dishes made from fresh, regional ingredients, ensuring a delightful dining experience. After a day of exploring, retreat to nearby accommodations that prioritize comfort and service, allowing you to relax and recharge for your next adventure in this enchanting destination.

Find the best pool hotels in Stockbridge

For travelers seeking a refreshing retreat in Stockbridge, these hotels offer inviting pool amenities that promise relaxation and leisure during your stay.

The Inn at Stockbridge

  • Why it's great: Travelers looking for a luxurious pool experience will find The Inn at Stockbridge to be an excellent choice. This 4-star hotel, with a perfect review rating of 10 out of 10, features a stunning outdoor pool that invites travelers to bask in the sun and take refreshing dips. The hotel’s tranquil ambiance is enhanced by its beautiful garden and terrace areas, creating a serene escape.
  • Other amenities: Guests can indulge in complimentary cooked breakfast daily, ensuring a delightful start to their day. The inn also offers designer toiletries and premium bedding for an extra touch of comfort. A fireplace adds a cozy atmosphere, and the option for in-room pets ensures that furry companions can join the fun. With free self-parking and air conditioning, convenience is a priority for all travelers.
  • Nearby attractions: Berkshire Theatre Festival - 1 mile, Housatonic River - 2 miles, Schantz Galleries - 2 miles

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

  • Why it's great: Ideal for those who appreciate a peaceful, intimate setting, The Stockbridge Country Inn features a delightful pool area complete with sun loungers. With a review rating of 9 out of 10 and a 4.5-star rating, this bed and breakfast offers a charming combination of luxury and comfort. Guests can enjoy a complimentary full breakfast, perfect for energizing before a day of exploration or relaxation by the pool.
  • Other amenities: The hotel is designed in a historic style, offering a cozy ambiance complemented by a fireplace. An onsite art gallery adds a unique cultural touch to the experience. Free WiFi and self-parking enhance traveler convenience, while the garden and terrace provide lovely spots for relaxation. Guests can also enjoy premium bedding, toiletries, and the option of a private chef for a special culinary experience during their stay.
  • Nearby attractions: Chesterwood - less than 1 mile, Schantz Galleries - 2 miles, Naumkeag Museum - 2 miles

The Red Lion Inn

  • Why it's great: Perfect for those who want to unwind by the water, The Red Lion Inn features an inviting outdoor pool complemented by sun loungers for ultimate relaxation. With a strong traveler review rating of 9 out of 10 and a 3.5-star rating, this historic hotel offers a charming atmosphere ideal for leisure seekers. Guests can enjoy 24-hour room service, making it easy to dine poolside or in the comfort of their rooms.
  • Other amenities: The hotel also boasts an onsite spa, perfect for indulging in a massage after a day by the pool. Evening entertainment options enhance the experience, while the beautiful garden and historic district location provide a picturesque backdrop. With complimentary WiFi and daily housekeeping, travelers enjoy comfort and convenience throughout their stay. The hotel also features a cozy fireplace area, ideal for relaxing evenings.
  • Nearby attractions: Housatonic River - less than 1 mile, Naumkeag Museum - less than 1 mile, Berkshire Botanical Garden - 2 miles

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice Property clean rooms walked the new footpath out back always enjoy the saltwater pool."
Dan 2-night trip
Posted 7 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"
Anne Marie 2-night trip
Posted 9 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 1 day ago
The Red Lion Inn
The Inn at Stockbridge

The Inn at Stockbridge

10/10 Excellent
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
Kimberly 1-night trip
Posted 4 days ago
The Inn at Stockbridge

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?
The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.
How much does a hotel with outdoor pool in Stockbridge cost?
Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $101 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Stockbridge for you.

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